Investing labor time in herbage measurements is important for precision pasture management. In this study, the labor input of three smart herbage measurement tools—multispectral imagery linked to an unmanned aerial vehicle (UAV), a semi-automated rising plate meter (RPM), and near-infrared reflectance spectroscopy (NIRS) of cut herbage samples—and of direct observation was modeled based on the REFA work element method. Three to five users were observed during work execution to identify best-practice workflows. Time measurements were conducted using video footage. The resulting standard times of work elements were used to model labor input for herbage measurements in different farm sizes (i.e., milking platforms of 6–100 ha) and subdivisions of a farm’s milking platform (i.e., 4–45 paddocks). Labor time requirement differed between the smart farming tools (0.7–5.9 h) depending on the farm size and milking platform scenario. The labor time requirement increased for all tools with an increase in farm size and was lowest for the RPM. For the UAV tool, it did not increase noticeably when the division of the milking platform changed. Nevertheless, the potential to save time was identified for the UAV and the NIRS. Therefore, the automation of certain steps in the workflows would contribute to sociotechnological sustainable pasture management.